Novel Ansa-Chain Conformation of a Semi-Synthetic Rifamycin Prepared Employing the Alder-Ene Reaction: Crystal Structure and Absolute Stereochemistry †
Abstract
:1. Introduction
2. Materials and Methods
3. Results
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Compound 3 | |
---|---|
Empirical formula | C45H62N4O15, CHCl3 |
Mr | 1018.35 |
T (K) | 100(1) |
Wavelength | CuKα (1.54178 Å) |
Crystal system | Orthorhombic |
Space group | P212121 |
a (Å) | 14.4057(4) |
b (Å) | 14.9409(3) |
c (Å) | 22.8735(7) |
α (°) | 90 |
β (°) | 90 |
γ (°) | 90 |
V, (Å3) | 4923.2(2) |
Z′, Z | 1, 4 |
ρcalc (Mg m−3) | 1.374 |
μ (mm−1) | 2.287 |
F(000) | 2152 |
Crystal colour, shape Size (mm) | Colourless, plate 0.251 × 0.250 × 0.071 |
Diffraction limit | 0.80 Å |
Coverage, % | 99.9 |
Friedel coverage, % | 81.0 |
Friedel fraction max % | 99.8 |
Reflections collected/unique | 26,683/10,050 |
Rint | 0.0406 |
Observed reflections, I > 2σ(I) | 9228 |
Tmin, Tmax | 0.748, 1.000 |
Data/restraints/parameters | 10,050/0/650 |
GOF, (S) on F2 | 1.035 |
R1 [I > 2σ(I)] | 0.0422 |
wR2 (all data) | 0.1140 |
Flack x parameter (refined) | −0.003(18) |
Flack x parameter (from 3814 quotients) | −0.009(9) |
Hooft y parameter | −0.008(6) |
Min/max residual density (e Å−3) | 0.658/−0.481 |
CCDC deposition number | 2,045,594 |
Torsion Angle | Compound 3 | Rifamycin O PUTDUD, 1 | Rifamycin S PAFRAP, 4 |
C2-N1-C15-C16 | −173.29(3) | −176.4 | −177.3 |
N1-C15-C16-C17 | 59.8(4) | 63.6 | 92.8 |
O3-C12-O5-C29 | −85.2(3) | −81.7 | −61.6 |
C12-O5-C29-C28 | 66.0(4) | 65.9 | −117.2 |
C21-C22-C23-C24 | 55.0(4) | 63.2 | 60.4 |
C20-C21-C22-C23 | 176.0(3) | −172.1 | −174.8 |
C25-C26-C27-C28 | −171.6(3) | 56.0 | −172.3 |
C16-C17-C18-C19 | 146.4(3) | 36.5 | 178.8 |
C17-C18-C19-C20 | −136.4(3) | −178.6 | −175.3 |
C18-C19-C20-C21 | −1.2(5) | 117.4 | −45.6 |
C19-C20-C21-C22 | 92.8(4) | 172.5 | −175.6 |
Intramolecular Contact Distance | Compound 3 | Rifamycin O PUTDUD, 1 | Rifamycin S PAFRAP, 4 |
O1······O2 | 2.436(4) | 2.538 | 2.566 |
O1······O9 | 7.622(4) | 4.300 | 7.245 |
O1······O10 | 6.906(4) | 2.912 | 6.205 |
O2······O9 | 8.276(4) | 3.613 | 6.166 |
O2······O10 | 7.811(4) | 3.980 | 7.836 |
O9······O10 | 2.711(4) | 2.702 | 2.689 |
C2······C33 | 3.474(5) | 6.601 | 6.314 |
C3······C33 | 3.383(5) | 6.442 | 5.858 |
D-H······A | d(D······H) | d(H······A) | d(D······A) | <(DHA) |
---|---|---|---|---|
O1-H1A······O2 | 0.96(8) | 1.54(8) | 2.436(3) | 154(7) |
O9-H9······O4′ | 0.73(6) | 2.10(6) | 2.750(4) | 149(6) |
O10-H10······O9 | 0.75(6) | 2.04(6) | 2.711(4) | 148(6) |
N1-H1B······O1 | 0.89(5) | 2.22(5) | 2.666(4) | 111(4) |
N1-H1B······O14 | 0.89(5) | 2.54(5) | 3.390(4) | 159(4) |
N1-H1A······N2 | 0.89(5) | 2.68(5) | 3.279(4) | 126(4) |
N3-H3······O11″ | 0.86(5) | 1.94(5) | 2.771(4) | 163(4) |
N4-H4······O4 | 1.00(5) | 1.60(5) | 2.595(4) | 171(4) |
Sample Availability |
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Frampton, C.S.; Gall, J.H.; MacNicol, D.D. Novel Ansa-Chain Conformation of a Semi-Synthetic Rifamycin Prepared Employing the Alder-Ene Reaction: Crystal Structure and Absolute Stereochemistry. Chemistry 2021, 3, 734-743. https://0-doi-org.brum.beds.ac.uk/10.3390/chemistry3030052
Frampton CS, Gall JH, MacNicol DD. Novel Ansa-Chain Conformation of a Semi-Synthetic Rifamycin Prepared Employing the Alder-Ene Reaction: Crystal Structure and Absolute Stereochemistry. Chemistry. 2021; 3(3):734-743. https://0-doi-org.brum.beds.ac.uk/10.3390/chemistry3030052
Chicago/Turabian StyleFrampton, Christopher S., James H. Gall, and David D. MacNicol. 2021. "Novel Ansa-Chain Conformation of a Semi-Synthetic Rifamycin Prepared Employing the Alder-Ene Reaction: Crystal Structure and Absolute Stereochemistry" Chemistry 3, no. 3: 734-743. https://0-doi-org.brum.beds.ac.uk/10.3390/chemistry3030052